Tales of the Audrey have put me in a reflective mood. I've been thinking about my calendar sync wars.
I've spent a lot of time and energy trying to get an integrated view of my work, personal, and other assorted calendars -- without putting all my personal life on the corporate server.
Ten years ago the answer seemed at hand. I could sync my Palm with Outlook at work, and with Palm desktop at hand. Alas, sync bugs did me in. The brass ring slipped from my fingers.
I settled for synchronizing KeySuite at work, and DateBk4/5 at home. So I had two calendars on one device, but they had nothing to do with one another. It really wasn't a great solution, but there was still hope.
Now I have an iPhone, but in many ways it's a step back from the Palm III. Heck, it's even regressing from iPhone 1.0; Apple recently pulled corporate Outlook support from its Windows MobileMe control panel. (A wikipedia article claims this is by design; the function won't be restored.)
All the solutions that now work for an iPhone either require extensive corporate support and wipe out your personal calendar (Exchange) , or they require synchronizing corporate calendars to an Internet service .
Corporations don't like sending corporate data to the net. With good reason. Imagine a billion dollar acquisition going down the tubes because someone left their phone on the bus, or accidentally made their net calendar public.
So why do corporations tolerate Blackberries? Because of a killer feature of the Blackberry (or is it an ActiveSync feature?) that Apple has emulated. If an iPhone is lost, it can be sent a remote instruction to wipe its Exchange server records. That's not possible if you sync Outlook to MobileMe, which is probably why Apple removed that feature.
So we see clearly now. We understand why something that's merely hard to do has become impossible Your work calendar, and your work contacts, don't belong to you -- even if you're the CEO. They belong to your corporation. Indisputably. Your corporation, who doesn't want to risk losing that data.
I could live with that if, say, work ran from 9-5 every day and we didn't have business travel.
Problem is, work and life aren't set like that any more. Today I started work at 9:30 and finished at 7:00 -- by choice. As long as I don't miss my meetings nobody cares too much when and where I work.
The downside of this flexibility is that work and family calendars mix all over the place. I need to have access to both ... all the time.
Oh, and like most oddball R&D types I don't fit the corporate rules for a Blackberry, so I can't even carry a BB for work and an iTouch for home.
This data ownership and life/work overlap problem is why, ten years after the Palm, we're moving backwards. We used to be able to "sneak" corporate calendars onto our Palms and MobileMe via Outlook and USB/serial data cables, but those options have gone away.
There's only one option now, the Exchange server option and over-the-air sync. That requires your corporate IT department's support, and if you go this route the only option for a personal calendar on the iPhone is MobileMess.
Or you can give up, embrace the public self, and put all your personal and family data on the work calendar -- but then you can't share that with your spouse and children. It becomes locked to the corporation.
I think the only plausible way forward is to push corporations to support iPhones with Exchange server (very hard) while also pushing Apple (much harder) to either fix MobileMe or give other vendors MobileMe's magic power to coexist with Exchange synchronized data.
I wonder what the gPhone does?
-- footnotes --
 Unless you also pay for a MobileMe account, but MobileMe doesn't support CalDAV or even iCal publication/subscription.
 Apple won't give 3rd party vendors access to the physical cable -- probably to protect their FairPlay franchise. So, unlike the Palm days, vendors can't create products to sync Outlook/Exchange data over the cable.
Update 12/23/08: See an earlier post with a similar theme.
Update 1/31/09: "Democratic Republics" never are. The same logic that can be applied to Citrix's "Project Independence". If we're going to have work/home calendar integration it will be entirely on the terms of the corporate IS department.